


Losing to Win

by Cipheral



Series: KakaGai 2019 [2]
Category: Naruto
Genre: Anal Sex, Flavored Lube, KakaGai Week 2019, M/M, Oral Sex, Riding, Rivals, Strap-Ons, Trans Hatake Kakashi, Trans Male Character, seriously im not fucking around, use enough lube when having sex people
Language: English
Status: Completed
Published: 2019-12-30
Updated: 2019-12-30
Packaged: 2021-02-27 16:07:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,739
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22039789
Author URL: https://archiveofourown.org/users/Cipheral/pseuds/Cipheral
Summary: Kakashi lost the latest challenge between himself and Gai, and now Gai gets to have some of his own fun. Luckily for Kakashi, the things he has planned for the two may have been worth losing the challenge for.
Relationships: Hatake Kakashi/Maito Gai | Might Guy
Series: KakaGai 2019 [2]
Series URL: https://archiveofourown.org/series/1583518
Comments: 3
Kudos: 78





	Losing to Win

**Author's Note:**

> Lads, this thing took me 3 fucking days to write, and set me behind even further in kakagai week. 5 days behind, hopefully the rest of these should be hammered out on time. It's Fine. 
> 
> Anyways take almost 5k of these two absolutely railing each other.

Out of all of the many, many things that Kakashi expected from losing his and Gai's latest challenge, this was not one of them. At the moment, Kakashi was sitting on one of Gai's dining room chairs, shoulders and arms tied to the back of the chair, keeping his back straight. His legs were tied to the two front legs of the chair as well, keeping him thoroughly pinned in place.

Tapping his foot as best as he could in his current position, Kakashi huffed impatiently. He was stuck there in his boxers and mask, Gai having gone out at some point for reasons he wouldn't divulge to Kakashi, leaving him tied up. He knew exactly what it was Gai had planned, and knew that this was a test of patience on his end, but none of that made it any less frustrating.

Kakashi tugged against his bindings, grimacing at the feeling of the rope rubbing against his wrists and ankles. He really hoped that he wouldn't be stuck like this for the entire penalty game of sorts. That may not be as fun as either of them anticipate.

As he heard the front door to Gai's apartment open, he let out another frustrated huff, loud enough for Gai to hear it as he made his way into his bedroom. Tilting his head back to look at his partner, Kakashi gave Gai a halfhearted glare.

“Sorry for making you wait, rival! I thought that this would be a bit more fun with... something new,” Gai said, setting down a plain black bag on his bed. He chose his words carefully at the end, seeming almost nervous as he began to remove his clothes.

“Is something wrong?” Kakashi asked, trying to scoot the chair closer unsuccessfully.

“No! Not at all,” he answered, much too quickly to ease any of Kakashi's worry.

Kakashi raised an eyebrow, leaning as best as he could in an attempt at seeing Gai's face. Gai stood facing away from him, also solely in his boxers now, ruffling around in the bag that he had tossed onto the bed earlier.

“Let me rephrase that, then: Why are you so nervous?” he tried again, giving up on trying to see Gai's face as the ropes tying him up rubbed uncomfortably once more.

Gai didn't answer for a moment, freezing in his movements. Slowly, he continued doing whatever it was that Kakashi _couldn't see_ , and spoke. “I was thinking of trying something new tonight, but I don't know if you'll be comfortable with it. I figured that it wouldn't be a total waste even if you didn't want to try it, so I did get everything for it anyways, but I cannot help but worry about how it will go over with you!” he said, false confidence seeping into his voice.

“Well, I won't know if I want to try it unless you tell me what it is you want to try,” Kakashi said, as bluntly as possible. He didn't want Gai to know the way that his heart jumped into his throat at the thoughtfulness, or the way his stomach tied itself up with anticipation and anxiety over the prospect of some new... something. He figured it was a new sex toy, but when it came to Gai, he really couldn't be sure on anything like that.

Still hiding something behind him, Gai turned around to face Kakashi, his face tinted red, struggling to make eye contact. “I want to ride you!” he said, face getting even more impossibly red as he blurted the simple admission out.

Kakashi stared at him for a long moment, blinking wordlessly at the fumbling, enthusiastic fool that stood in front of him.

“Gai,” he said, “I don't have a dick.”

“I know! I know, and I know that our current dildo situation wouldn't actually work very well for that, so-” Gai rambled, turning around and holding up what, at first glance, looked like a strappy mess of shiny fake leather and buckles. After a moment, Kakashi's brain finally caught up with him, and he realized that it was, in fact, a strap on harness.

“You went out and bought a strap on harness,” he said, once more doing his best to hide the way that his heart skipped at the prospect of using it.

Gai nodded, finally looking directly at Kakashi. He looked like he was about to explode with anticipation, and Kakashi was fairly certain that he was holding his breath while waiting for a proper response. Looking back at the harness in Gai's hand, he worried his bottom lip between his teeth, considering it.

“You know you're going to have to let me up from here so I can get that on comfortably, right? That tying me up like this just made more work for you?” he said, looking Gai in the eye.

“So you're okay with using it?” he asked, setting it down on the bed once more as he made his way over to Kakashi's back to undo the knots keeping him in place.

“If I wasn't I wouldn't have even suggested wearing it,” Kakashi muttered, rubbing his wrists once they were free. He continued as Gai circled around to undo his ankles. “Is it one that's got anything on the inside, or does it just have the dick on it?”

“Why don't you go look for yourself?” Gai said with a wink, rubbing Kakashi's ankles as he got the rope off.

Rolling his eyes, Kakashi stood up, wandering over to the edge of the bed and picking up the harness. It was heavier than he expected, but not anything that he couldn't get used to. Turning it over in his hands, he noticed that it did not, in fact, have anything on the inside of it. His eyes wandered over to the bag, eyebrow raising as he noticed it still had something within, the packaging creating an odd lump under the plastic.

“What else did you get?” he asked, not reaching for the bag quite yet. “Also, I thought this was supposed to be a penalty for losing the last challenge, not a reward.”

“That's for later! I also don't think you're going to be thinking this as a reward for very long,” Ga responded with a wink. “However, this _could_ be another challenge if we wanted to make it one...”

“I don't want to, so just tell me what you've got planned here. I'm getting impatient.”

Gai wrapped his arms around Kakashi's waist, pressing a kiss to his temple. Kakashi hummed lightly at the contact, pressing his back closer to Gai's chest. Gai's skin was warm against his own, causing him to shiver slightly as Gai began mouthing at his neck, pushing the bottom of his mask out of the way.

Kakashi turned around, tugging his mask down as Gai redirected his attention to his mouth, kissing him deeply. Gai's hands wandered from where they rested on Kakashi's waist, sliding under the waistband of his boxers, kneading his ass. Kakashi gasped into his mouth, pressing closer as Gai tried to pry him off him halfheartedly.

Gai pressed another couple of open mouthed kisses to Kakashi's jaw as he switched their positions, tugging him down as he sat down on the bed.

“So how's this going to work,” Kakashi panted, “What all do you want me to do? You're in control this time.”

Gai stared up at him for a long moment, trying to catch up with what was happening. “Put the harness on?” he said, the phrase coming out more like a question than an order. If there was one thing that he knew Kakashi was capable of, it was following orders, no matter where he was.

Reaching down, Kakashi lifted the strap on harness up, turning it around in his hands to see just how it worked. With a bit of Gai's help, he eventually got it on, the waist and leg straps comfortably tight, but not restricting. He didn't like the prospect of chafing, however, so he had foregone removing his boxers, which made it bunch the fabric up in a few places.

“How does it feel?” Gai asked, hands resting on Kakashi's hips as he walked close once more.

“It's... interesting, to say the least. Maybe I'll take these off next time we use this...” he muttered, tugging at the loose fabric around his legs. “Maa... I don't know how to feel about this. I'm willing to keep going, but you had better enjoy it this time, 'cause I don't know if we're going to be using this again.”

Gai's hands grabbed at Kakashi's ass once more, and he rested his forehead against his hip. “Of course, love. I can promise you that I won't be the only one who gets off tonight, at least. You'll like what I have planned for you, I hope. You may have to wait for it – in fact I know you're going to have to – but as they say: patience is a virtue!” he said, pressing a few pecks to the skin just above where his boxers waistband was bunched up due to the harness waistband.

Kakashi ran his fingers through Gai's hair, humming a bit in response. Of course the one who was about to get his ass wrecked would say that. He smiled a bit as Gai's eyes closed, his cheek resting against his thigh. Yeah, he could wait to get off so long as it meant that he could make Gai happy with what he got after winning the last challenge. In all honesty, he wasn't going to bitch about the circumstances he was in.

“Are we just using the one this came with, or do you want to pick a different dick?” Kakashi asked, tugging a bit at Gai's hair to get his attention.

Gai looked up at him, leaning back and resting his palms against Kakashi's thighs. His eyes flicked down to the strap on that was in front of him. Without giving Kakashi a proper response, he pressed his lips to the tip of the dildo, parting them as he sunk his mouth onto it while maintaining eye contact with Kakashi.

Kakashi sucked in a harsh breath through his nose, the hand he had in Gai's hair tightening involuntarily, tugging at the well maintained locks. Gai sank down until his nose was brushing the harness, staying there for a moment before slowly pulling off. He wiped his hand across his mouth to break the few strands of saliva that still connected his lips and Kakashi's dick, still making eye contact.

“This one. Got it,” Kakashi choked out, walking over to the bedside table to fish out the bottle of lube they had tucked away in the drawer. While he dug around, he heard Gai moving the bag off of the bed, tucking it away somewhere for later on. Finding the bottle under a few loose papers that had been tossed aside some while back, he also tugged a condom from the box tucked away at the back of the drawer.

When he turned around, Gai was back sitting on the edge of the bed, watching him with a strange look in his eyes.

“What's with that look?” Kakashi asked, tossing him the bottle of lube.

“I'm simply thinking about how enjoyable it's going to be to ride my wonderful boyfriend's dick,” Gai said, laughing a bit when Kakashi coughed, the tips of his ears turning bright red. “You'll probably be glad to hear, though, that half of the reason it took me so long to get back was because I spent a good while prepping myself in the living room before I left. I should still be fairly loose.”

Kakashi coughed into his shoulder again, his face burning. Gai was almost too much sometimes.

“Want me to prep just a bit more, so there's no worry?” he asked, the bed squeaking just a bit as he got up and walked over to Kakashi, grabbing his hands and pressing light kisses to the palms.

“Ideally, yes. I don't want this to hurt you. I know we've used toys before, but this is a little bit different than a vibrator,” Kakashi said, watching Gai press more kisses to the various scars on his hands, lips pressing gently against each knuckle. “Do you want me to take the mask off fully?”

Gai reached up, hooking his fingers under the mask that had been bunched up around Kakashi's neck and tugging it up and over his head. “There; now I'll be able to kiss you better,” he said, emphasizing his point by pressing a kiss to the little mole on Kakashi's chin.

Kakashi watched, in a bit of a daze, as Gai made his way back to the bed, uncapping the lube and pouring a generous amount over his fingers. On his knees, facing Kakashi, he reached his hand behind him, eyes slipping closed and mouth parting slightly as he stretched himself open.

The sight alone was enough to make Kakashi weak in the knees. His mouth felt very, very dry all of a sudden, and he licked at his lips, unable to take his eyes off Gai. While Gai had been the one receiving quite a few times in the past, Kakashi had never quite gotten to see him prepare himself like this. The heave of his chest when his breath hitched, the way his legs shook with the effort of keeping himself up, the _expressions_ that he made... it was driving Kakashi absolutely mad.

“Are you almost done there?” Kakashi asked, the question coming out slightly choked.

Gai, the bastard that he was, _laughed_ at that. Head falling forwards, his lips parted in a slight smile as he panted, he looked up at Kakashi. “Patience... is a virtue. And if you're able to be patient, and do as I ask, then you're going to like what else I've got in store,” he said, still working himself open.

“So this is a test?” Kakashi asked, pulling the chair he'd been seated on earlier over and taking a seat on it once more. “And all I have to do is follow orders?”

“That's all.”

“For once I can say that I don't think this is going to be as easy as it sounds.”

And by the gods, was he right about that. Gai continued stretching himself open, and all Kakashi could do was watch, shifting uncomfortably as his boxers dampened. It was a nearly impossible task, having to sit there and wait until he was called over. Kakashi was about to just give up and go over there when Gai finally, _finally_ , beckoned him over. All too enthusiastically, Kakashi hurried over, practically tossing the chair behind him as he got up.

“Lay down, on your back,” Gai instructed, getting up as Kakashi got into position.

Kakashi watched as Gai picked up the rope from earlier, and grimaced. “Maa... do we really have to use that?” he asked, rubbing at his wrists subconsciously.

Gai looked at him, a little bit startled, before setting it back down. “If it makes you uncomfortable, then no. I'll find something else to keep you down with,” he said, Kakashi's attention fully drawn once more.

So it was going to be like that, then? Kakashi let his head fall back against the pillows, his arms splayed out on either side of him. He may as well get comfortable now, because he was in for it when Gai got back with something softer.

Not ten seconds later, Gai returned, running his hand against Kakashi's legs as he parted them. He very aptly tied each ankle to either post attached to the foot board of his bed, moving up to Kakashi's left side. Pressing a kiss to his palm quickly, Gai made quick work of tying Kakashi's hands together above his head, securing them tightly to the headboard. Kakashi gave a quick, experimental tug before nodding in approval. He sure as hell wasn't getting out of that one in his current situation.

With Kakashi secured, Gai climbed onto the bed, straddling Kakashi's waist. He leaned forwards, kissing Kakashi, slotting their lips together easily. By the time that Gai pulled away, Kakashi's lips felt bruised. Kakashi rolled his shoulders, trying to catch him for one last peck, with no real luck.

Gai rested is hand on Kakashi's chest as he perched back on his haunches, keeping Kakashi pinned to the bed with no effort. Shifting back just a bit, Gai used his free hand to line the dildo up with his ass, slowly sinking down. While Kakashi couldn't feel anything other than the strap on shifting just slightly as Gai moved inch by inch, he swore that he was about to pass out from the sight before him.

He had, in the past, fucked Gai with a dildo, but that had been an incredibly different scenario. He hadn't been tied up, and he had been manoeuvring the dildo with his hand, not his hips. There was also the fact that he now realized why Gai liked it so much when he rode him.

Gai's eyebrows were pinched, a concentrated expression tugging at his features. As he finally bottomed out, his face relaxed, eyes closing for a brief moment.

“Holy shit,” Kakashi breathed out, forgetting his hands were tied for just a second as he tried to reach out and touch Gai's face.

Gai let a huff of laughter out, one corner of his mouth quirking up in a half smile. He cracked his eyes open, scanning Kakashi's face. “I think I could get used to this. I quite like the way you look under me like this,” he said, running his hands over Kakashi's abdomen and chest, fingers brushing lightly over the faded scars that sat just a few centimetres under his nipples.

Kakashi shuddered at the light touch. The feeling was slightly numbed, the nerves where the scars were weren't quite back to how they were before surgery, and Kakashi wasn't actually sure they'd ever be. Not that he minded, though. As Gai's fingertips brushed over his nipples, he sucked in a sharp breath through his nose. His chest was _definitely_ sensitive enough, even with the numbed scars.

Carefully, Gai lifted his hips, still getting used to the stretch, before pausing, looking Kakashi dead in the eyes and _slamming_ his hips down. Kakashi gasped, hands tugging against the fabric that was keeping them secured. He wanted so badly to hang onto Gai's hips as he continued fucking himself on Kakashi's dick.

Kakashi's hips bucked up, meeting Gai's downward thrusts as best as he could while tied up. He would be lying if he were to say that this wasn't turning him on to absolutely incredible lengths.

After a few minutes, Gai's thrusts got more erratic and he changed the pace to make up for it. Instead of the hard, fast thrusts, he took it deep, rolling his hips and grinding down, the dildo hitting all the right places, it seemed, as his head tipped back and mouth fell open. Kakashi stilled his hips, letting Gai take his time and move things along as he wanted now. He wasn't too sure he would be able to do much more than stare, anyways. With the way that Gai leaned back, changing the angle of the thrusts, and the way he moaned Kakashi's name, Kakashi was completely enraptured.

Gai was close, Kakashi knew that, and he figured that he had been good at doing what he was told up until this point. So, watching Gai's face carefully, he waited until he saw the telltale sign that he was on the edge. When Gai bit his bottom lip, Kakashi thrust upwards, hard. With a choked gasp, Gai's supporting hand grabbed tight to the blankets beneath them, his other hand flying up to his mouth to muffle the cry that spilled out as Kakashi continued to thrust, fucking him through his orgasm.

Kakashi stilled his hips, grimacing slightly at the cum that was cooling on his stomach. Tugging at his hands once more, he let out a frustrated sigh. This is why he wasn't exactly a fan of being tied up; he couldn't actually do any clean up, or even just hold Gai as he came down from his orgasm. It was annoying.

“You alright? That seemed pretty intense,” Kakashi said, letting his arms go slack in their bindings.

“I'm fine. I definitely think that we're going to be doing this again some day,” Gai panted, his voice rough.

“Despite the fact I'm currently frustrated with my own lack of orgasm, yeah. That... was good. I think I finally get why you like it so much when I ride you.”

Gai laughed at that, pulling himself off of Kakashi with a wince and flopping off to the side to gather himself once more. “I'll untie you, and you can take that off if you want?” he said, standing after a few moments on shaky legs.

“That sounds great, actually,” Kakashi said, trying to keep his tone light as his frustration grew.

With his hands free, Kakashi didn't even wait for Gai to untie his ankles before reaching for the buckles on the harness. He tugged the harness off, tossing it to the side, and leaned forwards to help speed up the process of undoing his ankles. Once fully free, Kakashi tugged his boxers off, laying back on the bed once more as Gai grabbed the bag from earlier.

“So, what did you get that you think I'm going to thoroughly enjoy?” he asked, “You've made me wait this long, and if I've gotta wait much longer I may take it upon myself to finish the job you started.”

Hand in the bag, Gai grinned. “Well, this is _technically_ still a reward for me for winning the last challenge, but...” he said, trailing off as he pulled something out of the bag.

With the bag discarded, Kakashi raised an eyebrow at the bottle in Gai's hand. “More lube? Gai, you do realize we still have, like, half of the other bottle left, right?” he said, “We didn't need-”

“It's flavoured, tingling lube, actually,” Gai said, cutting Kakashi off mid sentence.

Kakashi stared for a long moment, head spinning as he processed what Gai just said. “Oh,” he choked out. Clearing his throat, he continued, “I guess that that's a, uh, good purchase then.”

“Like I said, this is still _kinda_ still working off the fact I won the last challenge, but you're probably going to enjoy it as much, if not more,” Gai said, sitting down on the edge of the bed and leaning over Kakashi to press his lips to his forehead.

Kakashi hummed, his eyes slipping closed as Gai pressed light kisses all over his face. From his nose, to his eyelids, to his cheeks, chin, and lips, Gai peppered his face with pecks before slowly working lower. His jaw, neck, and collarbones were given open mouthed kisses, a few light nips making Kakashi squirm under the attention. The kisses didn't stop there, however, and Kakashi gasped when Gai took one of his nipples into his mouth, dragging his teeth over it lightly. It was only when Gai reached Kakashi's stomach that he stopped, realizing that he hadn't cleaned up before.

“Whoops,” Gai said, getting up quickly, hurrying to the washroom that was across from his room, and getting a wet cloth. With a gentle touch, he wiped Kakashi's stomach down, earning a light chuckle from him.

“So excited to show me what you've got planned that you forgot about the mess you made... That's unlike you,” Kakashi said, reaching up and caressing Gai's face, sliding his fingers into his hair. “You better be right about how much I'm going to like this because if you stall any longer...” he trailed off, giving a light tug on his hair.

Gai's eyes fluttered closed at the tug. Shaking his head, he set the cloth on the bedside table, going back to making his way down Kakashi's body. His lips pressed to each of his hips, and that was when he changed their positions. Kakashi sat up more, using the pillows behind him to support his lower back, but was gently pushed back down by Gai. Quirking an eyebrow at him, Kakashi let Gai manoeuvre him where he wanted him to be.

As it turned out, Gai wanted Kakashi to stay on his back, with one leg over Gai's shoulder, and a good few pillows under his back for support. Kakashi watched as Gai popped open the bottle of lube, putting it up to his nose to sniff it – which earned a chuckle from Kakashi – before pouring a generous amount on his fingers.

Kakashi's breath hitched as Gai's fingers dripped some of the lube onto him, the sensation of the tingling foreign to him. Things got even stranger feeling when Gai pressed his fingers against his folds, rubbing the slick, strange lube around and spreading the tingling sensation further.

Removing his fingers, Gai ducked his head down at long last, pressing the flat of his tongue against his hole, just barely dipping the tip in as he licked upwards. Swirling his tongue around Kakashi's clit, he repeated the licking motion a couple of times, riling Kakashi up more and more. It was only when Kakashi lightly kicked his heel against Gai's back did he pick up the pace, pressing his tongue deep, practically burying his face in him.

He drew his tongue out slowly, swirling it around before diving back into Kakashi's soaking wet folds. Once satisfied with the noises that Kakashi had begun to make, he drew back, using one hand to gently part his lips, and the other to pour another liberal amount of lube onto him. Closing the bottle, Gai tossed it aside, ducking his head down once more.

Being mindful of his teeth, Gai carefully sucked at Kakashi's inner lips, tongue occasionally darting out to catch some of the lube that was now slowly dripping around his mouth. Kakashi squirmed against him, panting hard, and that was when Gai knew it was time to hurry this up. Kakashi wasn't a patient man, and the fact that he hadn't just grabbed onto him and started riding his face yet was a miracle in and of itself.

So he changed tactics once more. Reverting back to the deep licks, Gai let out a moan while his mouth was pressed wide against Kakashi, earning himself another light kick in the back from Kakashi's heel. On one particular lick, as he drew his tongue out, he shifted his mouth, pressing his tongue hard against Kakashi's clit, which got the exact reaction he expected.

“Fucking hell, Gai-!” Kakashi said, hands flying down to grab at Gai's hair.

From that point on, Kakashi was holding Gai fast and hard against him. Gai's tongue suctioned against his clit, giving him a bit of leverage to wrap his lips around it properly, sucking hard as Kakashi rode his mouth.

With a shout that faded into a whine, Kakashi came, Gai continuing to eat him out through his orgasm.

Setting his legs back down on the bed, Gai reached over and grabbed the cloth from the bedside table once more, using it to gently wipe down Kakashi's groin and thighs.

“Was I right?” he asked, grinning to himself.

Kakashi, who had tossed his arm over his face, groaned tiredly in response. With both of them cleaned up, Gai lay down next to Kakashi resting his head on his chest.

Cracking one eye open, Kakashi glanced down at his boyfriend. “If I didn't still have my pride intact, I'd say I have to lose challenges more often,” he grumbled, rolling over and shifting down so that they were facing each other. Gai leaned forwards and pressed a kiss to the tip of Kakashi's nose, smiling tiredly at him.

“If you lost more, then this wouldn't be as fun, I think,” he said, pulling Kakashi closer with an arm tossed over his waist.

Kakashi didn't answer, really, only letting out a hum as he closed his eyes, pressing his forehead against Gai's and slotting their legs together.

However, as Gai pressed one final kiss to the corner of his mouth, he had to admit that he agreed.

It's no fun if he doesn't earn it, first.

**Author's Note:**

> Feel free to send me a DM or ask on tumblr @aroneji (art/writing) or @byakuboy (naruto only blog)!


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